Alternating and semi-alternating poly(ester-anhydride) copolymers
A copolymer characterized by alternating or semi-alternating ester and anhydride bonds, methods for its production and use thereof, particularly as a carrier for drug delivery, are described herein.
1. A poly(ester-anhydride) copolymer having alternating or semi-alternating ester and anhydride bonds of Formula (1)
wherein R′ and R″ are independently selected from linear or branched C 1 -C 40 alkyl, C 2 -C 40 alkenyl, and C 2 -C 40 alkynyl, and wherein x and y, independently for each occurrence, is an integer selected from 1 and 2, and n is an integer from about 2 to about 1,000.
2. The copolymer of claim 1 , wherein R′ is a branched C 2 -C 40 alkenyl comprising a C 1 -C 10 to alkyl-C 2 -C 20 alkenyl, wherein the C 1 -C 10 to alkyl is α to the —O— of the ester bond.
3. The copolymer of claim 2 , wherein R′ is a C 6 alkyl-C 11 alkenyl.
4. The copolymer of claim 1 , wherein R″ is a linear C 4 -C 22 alkyl.
5. The copolymer of claim 4 , wherein R″ is a linear C 8 alkyl.
6. The copolymer of claim 1 , formed by monomers of Formulae (3) and (4):
wherein R′ and R″ are as defined in claim 1 .
7. The copolymer of claim 6 , wherein the molar ratio of the monomers of Formula (3) to the monomers of Formula (4) ranges from 2:1 and 1:2.
8. The copolymer of claim 7 , wherein the molar ratio of the monomers of Formula (3) to the monomers of Formula (4) is 1:1, and wherein the copolymer comprises a repeating unit comprising a monomer of Formula (3) and a monomer of Formula (4) linked by an ester bond.
9. The copolymer of claim 8 comprising an anhydride bond between repeating units.
10. The copolymer of claim 6 , wherein R′ is a branched C 2 -C 40 alkenyl comprising a C 1 -C 10 alkyl-C 2 -C 20 alkenyl, wherein the C 1 -C 10 alkyl is α to the —O— of the ester bond.
11. The copolymer of claim 10 , wherein R′ is a C 6 alkyl-CH 11 alkenyl.
12. The copolymer of claim 6 , wherein R″ is a linear C 4 -C 22 alkyl.
13. The copolymer of claim 12 , wherein R″ is a linear C 8 alkyl.
14. The copolymer of claim 6 , wherein the monomers of Formula (3) comprise ricinoleic acid and the monomers of Formula (4) comprise sebacic acid.
15. The copolymer of claim 1 comprising less than 10% of two or more consecutive anhydride bonds between the monomeric units.
16. The copolymer of claim 1 which is stable for at least 6 months at room temperatures.
17. A composition comprising the copolymer of claim 1 and at least one agent.
18. The composition of claim 17 , wherein the at least one agent is a pharmaceutical agent, a diagnostic agent, a cosmetic agent or a nutraceutical agent.
19. The composition of claim 18 , wherein the at least one agent is a pharmaceutical agent and wherein the composition is used as a medicament or device for therapy.